Some New Aspects of Chlorination of Fullerenes

Troshin, Pavel A.; Popkov, O.; Lyubovskaya, R.N.

doi:10.1081/fst-120021142

Cited by 41 publications

(50 citation statements)

References 27 publications

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“…This appears to be connected with the fullerene cage destruction prompted by massive chlorination, as mentioned above. The first individual chloride, C 60 Cl 6 , was obtained two years later [18], and this remains the most studied representative of the family [19,20]. C s symmetry was assigned to this chloride, which is consistent with the symmetry of the C 60 Cl 6 species given in Fig.…”

Section: Concluding Remarks: a Little About C 60 Chlorinationmentioning

confidence: 94%

“…10a) and C 60 Cl 6 ( Fig. 10b) (c) is suggested on the basis of experimental data [19,20]. Small black balls indicate carbon atoms, while light blue and green balls show fluorine and chlorine atoms, respectively contiguity of chlorine addition is terminated at the sixth step and subsequent 1,2-additions occur quite far from the first six atoms (see Fig.…”

Section: Concluding Remarks: a Little About C 60 Chlorinationmentioning

confidence: 96%

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Computational synthesis of C60 cyano- and azopolyderivatives

Sheka

2011

J Mol Model

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The cyanation of C(60) to C(60)(CN)(18) and the aziridination of C(60) to C(60)(NH)(9) were studied by an unrestricted broken spin symmetry Hartree-Fock approach implemented in semiempirical codes based on the AM1 technique. The calculations focused on the successive addition of CN and NH moieties to the fullerene cage following the identification of the target cage atoms as those with the highest atomic chemical susceptibilities calculated at each step. The results obtained were analyzed from the viewpoint of the parallelism between these derivatives as well as C(60) fluorides and hydrides. The difference between the first-stage C(60) chlorination and other sterically free processes is discussed.

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Section: Concluding Remarks: a Little About C 60 Chlorinationmentioning

confidence: 94%

Section: Concluding Remarks: a Little About C 60 Chlorinationmentioning

confidence: 96%

Computational synthesis of C60 cyano- and azopolyderivatives

Sheka

2011

J Mol Model

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“…However, it should be noted that phenyl deriva tives of fullerenes are formed as by products. 15 Rather recently, 16 the reactions of C 60 with ICl, ICl 3 , and KICl 4 in 1,2 dichlorobenzene have been examined. The preparation of chlorofullerenes with compositions ranging from C 60 Cl 6 to C 60 Cl 26 was reported, but these chlorides were not adequately characterized as indi vidual compounds.…”

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confidence: 99%

Synthesis and structures of C60 fullerene chlorides

et al. 2005

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Systematic study of chlorination of fullerene C 60 with inorganic chlorides SbCl 5 , VCl 4 , MoCl 5 , and KICl 4 was carried out. Higher chlorofullerenes, viz., T h C 60 Cl 24 , C 60 Cl 28 , C 2 C 60 Cl 30 , and D 3d C 60 Cl 30 , can be prepared depending on the temperature and time of chlorination. The molecular and crystal structures of C 60 Cl 24 •VOCl 3 , C 60 Cl 30 •2CS 2 , and C 60 Cl 30 O 1.22 were determined by single crystal X ray diffraction. Fullerenes C 60 Cl 28 and C 2 C 60 Cl 30 were shown to be only kinetically stable, whereas D 3d C 60 Cl 30 is a thermodynami cally stable product. Transformations of less chlorinated fullerenes into more chlorinated products are accompanied by substantial changes in the addition patterns.Until recently, fullerene chlorides have been studied in much less detail than fluorides or bromides. Numerous fluorofullerenes with the composition C 60 F n (n = 2-48) are known, 1 whereas data for fluorinated fullerene C 70 are scarce. 2,3 Properties of fullerene bromides have not been adequately studied because of their low thermostability and poor solubility. However, reliable structural data have been obtained for many of them (C 60 Br 6 , C 60 Br 8 , C 60 Br 24 , C 70 Br 10 , and C 78 Br 18 ). 4-6Until recently, the published data for chlorofullerenes have been contradictory. The reaction of solid fullerene C 60 with liquid chlorine at -36 °C afforded 7 mixtures of chlorides with molecular formulas C 60 Cl 12-15 . Chlorina tion of fullerene C 60 in a flow of chlorine at 250 °C pro duced 8 a sample, whose composition corresponded to C 60 Cl 24 (elemental analysis data). The IR spectrum of this sample contained broad absorption bands, which was indicative of the formation of a mixture of chlorides rather than an individual compound. An assumption 9 that the product prepared in a flow of chlorine at 325 °C is isostructural with the bromide T h C 60 Br 24 was not con firmed experimentally because only broad absorption bands were observed in the IR spectra. A product with the composition C 60 Cl 24 , which was also synthesized by di rect chlorination of fullerene, was studied based on elec tronic absorption spectra, which demonstrated 10 that the geometry of this chloride cannot be described by the mo lecular symmetry T h .The chlorination product formed upon UV irradiation of a solution of fullerene C 60 in CCl 4 contained chloro fullerene C 60 Cl 24 , as followed from mass spectrometric analysis. 11 However, no evidence was presented that it was pure C 60 Cl 24 that has been synthesized. MALDI mass spectrometric studies of reaction products prepared by UV irradiation of a mixture of C 60 with liquid chlorine revealed 12 several higher chlorofullerenes containing up to 32 chlorine atoms per C 60 fullerene cage.Reliable data on the composition and addition pat terns are available for two chlorofullerenes, viz., C 60 Cl 6 13 and C 70 Cl 10 , 14 which were prepared by the reactions of C 60 or C 70 , respectively, with iodine monochloride in benzene and were characterized by 13 C NMR...

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“…S6, ESIw). 12 The whole set of the NMR, UV-VIS and FT-IR spectroscopic data conform with the C s symmetrical molecular structures of compounds 1a-b shown in Scheme 1. At the same time, these data provide more solid support for the C s molecular structure of the precursor chlorofullerene C 70 Cl 8 in addition to the optical UV-VIS-IR data reported previously.…”

mentioning

confidence: 99%